Style 911: How Do I Wear Denim-On-Denim Without Looking Like A Prisoner?

I’ve been noticing a lot of head-to-toe denim in magazine pages. I thought this was a no-no, but I’m a little curious about the trend. Do you have any advice on how to make this look chic? – Jennifer

Denim-on-denim used to be a cardinal sin amongst the fashionable (too bad my 12-year-old self didn’t know that), but now it’s one of the biggest trends for spring. But you must tread lightly because no one wants to look like a farmer or prisoner walking the streets. After the jump, we give you tips for wearing a denim shirt with jeans.

AE Chambray Western Shirt, $44.50, American Eagle Outfitters

The top should be a light to medium wash. It should also fit just right — not too tight or too loose.

Left: Real Straight Jeans (Dark Wash), $69.50, Gap
Right: Long & Lean Jeans (Dark Wash), $69.50, Gap

The jean can be any fit you prefer, but should definitely be darker than the top. You can also get away with a pair of true black jeans.

Wide Jeans Belt, $39.50, Loft

A wide leather or suede belt is absolutely essential to break up the top and bottom.

Maria Sharapova by Cole Haan Air Bacara Flat, $138, Piperlime

Flat shoes are best, but you can also wear a pair of simple pumps.

Left: Deux Lux Woven Messenger, $120, Rumor
Right: Dixie Messenger, $89.50, The Sak

Wear a purse that is visually interesting, but doesn’t compete with your overall look.